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Showing metabocard for Tyramine (HMDB0000306)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:51 UTC
HMDB IDHMDB0000306
Secondary Accession Numbers
  • HMDB00306
  • HMDB0062629
  • HMDB62629
Metabolite Identification
Common NameTyramine
DescriptionTyramine is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals. Tyramine is a biomarker for the consumption of cheese
Structure
Data?1676999681
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000306 (Tyramine)


  Mrv1652306232000432D          

 10 10  0  0  0  0            999 V2000
   -2.0087   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7231   -0.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4377   -1.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4377   -2.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -2.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522   -2.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.7820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000306 (Tyramine)

HMDB0000306
     RDKit          3D
Tyramine
 21 21  0  0  0  0  0  0  0  0999 V2000
    3.5632    0.7281    0.4180 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206    0.7710    0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -0.2938   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415   -0.3037   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -1.0573    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -1.0523    0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746   -0.2739   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569   -0.2606   -0.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848    0.4803   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6976    0.4720   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    0.6612   -0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795   -0.1155    0.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    1.7670    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.6173    1.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692   -1.2758   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -0.1152   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0902   -1.6570    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -1.6462    1.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6799    0.3961    0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    1.0933   -1.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666    1.0649   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  END
Download

3D SDF for HMDB0000306 (Tyramine)


  Mrv1652306232000432D          

 10 10  0  0  0  0            999 V2000
   -2.0087   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7231   -0.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4377   -1.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4377   -2.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -2.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522   -2.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.7820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000306

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2

> <INCHI_KEY>
DZGWFCGJZKJUFP-UHFFFAOYSA-N

> <FORMULA>
C8H11NO

> <MOLECULAR_WEIGHT>
137.179

> <EXACT_MASS>
137.084063979

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.332804080654203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-aminoethyl)phenol

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
0.6797131598312175

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.410817992116419

> <JCHEM_PKA_STRONGEST_BASIC>
9.663317955732815

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
41.267300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tyramine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000306 (Tyramine)

HMDB0000306
     RDKit          3D
Tyramine
 21 21  0  0  0  0  0  0  0  0999 V2000
    3.5632    0.7281    0.4180 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206    0.7710    0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246   -0.2938   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415   -0.3037   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525   -1.0573    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0422   -1.0523    0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746   -0.2739   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569   -0.2606   -0.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848    0.4803   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6976    0.4720   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    0.6612   -0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795   -0.1155    0.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8011    1.7670    0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.6173    1.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9692   -1.2758   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -0.1152   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0902   -1.6570    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -1.6462    1.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6799    0.3961    0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742    1.0933   -1.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666    1.0649   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  END
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PDB for HMDB0000306 (Tyramine)

HEADER    PROTEIN                                 23-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-20         0                                  
HETATM    1  C   UNK     0      -3.750  -2.230   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.083  -1.460   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.417  -2.230   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.417  -3.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.083  -4.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.750  -3.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.751  -4.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.416  -1.460   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.082  -2.230   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.251  -1.460   0.000  0.00  0.00           N+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0000306 (Tyramine)

COMPND    HMDB0000306
HETATM    1  N1  UNL     1       3.563   0.728   0.418  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.121   0.771   0.549  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.525  -0.294  -0.320  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.042  -0.304  -0.231  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.653  -1.057   0.692  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.042  -1.052   0.759  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.775  -0.274  -0.119  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.157  -0.261  -0.063  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.085   0.480  -1.043  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.698   0.472  -1.105  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.865   0.661  -0.589  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.979  -0.116   0.882  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.801   1.767   0.159  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.879   0.617   1.607  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.969  -1.276  -0.026  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.865  -0.115  -1.373  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.090  -1.657   1.369  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.588  -1.646   1.486  1.00  0.00           H  
HETATM   19  H9  UNL     1      -4.680   0.396   0.513  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.674   1.093  -1.734  1.00  0.00           H  
HETATM   21  H11 UNL     1      -0.167   1.065  -1.831  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3   13   14
CONECT    3    4   15   16
CONECT    4    5    5   10
CONECT    5    6   17
CONECT    6    7    7   18
CONECT    7    8    9
CONECT    8   19
CONECT    9   10   10   20
CONECT   10   21
END
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SMILES for HMDB0000306 (Tyramine)

NCCC1=CC=C(O)C=C1
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INCHI for HMDB0000306 (Tyramine)

InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-(p-Hydroxyphenyl)ethylamineChEBI
4-Hydroxy-beta-phenylethylamineChEBI
4-HydroxyphenethylamineChEBI
4-HydroxyphenylethylamineChEBI
beta-(4-Hydroxyphenyl)ethylamineChEBI
p-(2-Aminoethyl)phenolChEBI
p-HydroxyphenethylamineChEBI
p-HydroxyphenylethylamineChEBI
p-TyramineChEBI
TyraminChEBI
4-Hydroxy-b-phenylethylamineGenerator
4-Hydroxy-β-phenylethylamineGenerator
b-(4-Hydroxyphenyl)ethylamineGenerator
Β-(4-hydroxyphenyl)ethylamineGenerator
2-(4'-Hydroxyphenyl)ethylamineHMDB
2-(4-Hydroxyphenyl)ethylamineHMDB
4-(2-Aminoethyl)-phenolHMDB
4-(2-Aminoethyl)-phenol(thyramin)HMDB
4-(2-Aminoethyl)phenolHMDB
4-Hydroxy-benzeneethanamineHMDB
a-(4-Hydroxyphenyl)-b-aminoethaneHMDB
alpha-(4-Hydroxyphenyl)-beta-aminoethaneHMDB
p-(2-Aminoethyl)-phenolHMDB
p-beta-AminoethylphenolHMDB
p-Hydroxy-b-phenethylamineHMDB
p-Hydroxy-b-phenylethylamineHMDB
p-Hydroxy-beta-phenethylamineHMDB
p-Hydroxy-beta-phenylethylamineHMDB
SystogeneHMDB
Tenosin-wirkstoffHMDB
TocosineHMDB
Tyramine baseHMDB
TyrosamineHMDB
UteramineHMDB
Para-tyramineHMDB
4 HydroxyphenethylamineHMDB
2-(4-Hydroxyphenyl)ethanamineHMDB
2-(4’-hydroxyphenyl)ethylamineHMDB
p-Hydroxy-β-phenylethylamineHMDB
p-Β-aminoethylphenolHMDB
Α-(4-hydroxyphenyl)-β-aminoethaneHMDB
Chemical FormulaC8H11NO
Average Molecular Weight137.179
Monoisotopic Molecular Weight137.084063979
IUPAC Name4-(2-aminoethyl)phenol
Traditional Nametyramine
CAS Registry Number51-67-2
SMILES
NCCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
InChI KeyDZGWFCGJZKJUFP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • 2-arylethylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial applicationIndirect biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point164 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.4 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg129.74430932474
[M+H]+Baker123.42730932474
[M-H]-Not Available129.744http://allccs.zhulab.cn/database/detail?ID=AllCCS00000289
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.72 g/LALOGPS
logP-0.14ALOGPS
logP0.68ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)9.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.27 m³·mol⁻¹ChemAxon
Polarizability15.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.67931661259
DarkChem[M+H]+127.67931661259
DarkChem[M-H]-125.18231661259
DarkChem[M-H]-125.18231661259
AllCCS[M+H]+129.94632859911
AllCCS[M-H]-130.13932859911
DeepCCS[M+H]+129.31930932474
DeepCCS[M-H]-125.54130932474
DeepCCS[M-2H]-162.94430932474
DeepCCS[M+Na]+138.19630932474
AllCCS[M+H]+129.932859911
AllCCS[M+H-H2O]+125.332859911
AllCCS[M+NH4]+134.332859911
AllCCS[M+Na]+135.532859911
AllCCS[M-H]-130.132859911
AllCCS[M+Na-2H]-131.932859911
AllCCS[M+HCOO]-133.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TyramineNCCC1=CC=C(O)C=C12555.8Standard polar33892256
TyramineNCCC1=CC=C(O)C=C11494.4Standard non polar33892256
TyramineNCCC1=CC=C(O)C=C11432.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tyramine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCN)C=C11485.0Semi standard non polar33892256
Tyramine,1TMS,isomer #2C[Si](C)(C)NCCC1=CC=C(O)C=C11664.1Semi standard non polar33892256
Tyramine,2TMS,isomer #1C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C=C11639.9Semi standard non polar33892256
Tyramine,2TMS,isomer #1C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C=C11664.3Standard non polar33892256
Tyramine,2TMS,isomer #1C[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C)C=C11761.8Standard polar33892256
Tyramine,2TMS,isomer #2C[Si](C)(C)N(CCC1=CC=C(O)C=C1)[Si](C)(C)C1852.8Semi standard non polar33892256
Tyramine,2TMS,isomer #2C[Si](C)(C)N(CCC1=CC=C(O)C=C1)[Si](C)(C)C1897.7Standard non polar33892256
Tyramine,2TMS,isomer #2C[Si](C)(C)N(CCC1=CC=C(O)C=C1)[Si](C)(C)C1971.0Standard polar33892256
Tyramine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C11880.3Semi standard non polar33892256
Tyramine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C11853.5Standard non polar33892256
Tyramine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C11760.0Standard polar33892256
Tyramine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCN)C=C11742.9Semi standard non polar33892256
Tyramine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCC1=CC=C(O)C=C11883.2Semi standard non polar33892256
Tyramine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12130.0Semi standard non polar33892256
Tyramine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12122.0Standard non polar33892256
Tyramine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12045.9Standard polar33892256
Tyramine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2249.5Semi standard non polar33892256
Tyramine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2313.5Standard non polar33892256
Tyramine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CCC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2132.1Standard polar33892256
Tyramine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12548.6Semi standard non polar33892256
Tyramine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12454.0Standard non polar33892256
Tyramine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12121.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tyramine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-2900000000-273503edc6a220e152b62014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyramine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-2900000000-80980d19fa83d4b86f912014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyramine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9700000000-78d2ae48da1eee18358e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyramine EI-B (Non-derivatized)splash10-001i-9200000000-50c21473a7d48011358c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyramine EI-B (Non-derivatized)splash10-00di-1900000000-9b1000a8978b57919c352017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyramine GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-273503edc6a220e152b62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyramine GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-80980d19fa83d4b86f912017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyramine GC-EI-TOF (Non-derivatized)splash10-00di-9700000000-78d2ae48da1eee18358e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tyramine GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-69892c95ab2778a208b32017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9600000000-1d5276a762318a00832d2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyramine GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-7900000000-8f3b164f36bc5a4df4d72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyramine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyramine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tyramine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-053r-9500000000-6deb2b5d214f768ca4482014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine , negative-QTOFsplash10-000i-0900000000-066947a256844eb6cbdc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine 35V, Negative-QTOFsplash10-000i-0900000000-4b0f190d7304f2cec82d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine 20V, Negative-QTOFsplash10-0a4i-0900000000-2feedb2abf4fe54134522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine 10V, Negative-QTOFsplash10-052r-0900000000-e67940e0a4f0f1b565c42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine 40V, Negative-QTOFsplash10-00lr-9400000000-47a2e802a22167ed8a632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-0900000000-3229081a448a277191a22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004l-9300000000-e2fc12d41e4c40a9a2962012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9000000000-92f0b12d0a64443cede82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine EI-B (Unknown) , Positive-QTOFsplash10-001i-9200000000-50c21473a7d48011358c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-000i-0900000000-d7e9a8705227b4504c5c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0006-9000000000-3f02b334907c40a8315c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-00di-0900000000-e98b3afc6fad78d45d382012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-001i-0900000000-54239e66d89de3096ca82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0079-0902000000-f09759fc06ef461f3aa52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0006-9000000000-9ffe6ee0ce68182216f72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-00di-0900000000-020a5decfb44fc4f97df2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-004i-0930000000-32ccc375e75dbab3195c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-00di-0900000000-51c6cc08017f1672b7912012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00di-1900000000-55c25dd64462c06c53162012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0f96-9500000000-83a70aec6da00b51a6df2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-004i-9100000000-5f044e831c0d2db255fa2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-004i-9000000000-99edae3913507430bf9f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-00di-4900000000-8944003750ac547c20242012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-00e85becc8cfc59bdb102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tyramine LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-58e8539844dcdbc977cc2017-09-14HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Medulla
  • Brain
  • Fibroblasts
  • Intestine
  • Liver
  • Neuron
  • Placenta
  • Platelet
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0095 +/- 0.0021 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00049 +/- 0.00037 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.30-2.54 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.91 +/- 0.39 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.10 +/- 0.54 umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected and Quantified0.33 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.36-0.70 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.38 (0.27-0.52) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
UrineDetected and Quantified4.296 +/- 3.675 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified0.237 (0.2-0.275) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<0.556 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.33-0.60 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.38 (0.23-0.78) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified0-86 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0017 +/- 0.00088 uMAdult (>18 years old)Both
Cirrhosis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Bothceliac disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn disease		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specifiedceliac disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Treated celiac disease		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer		 details
UrineDetected and Quantified7.003 +/- 6.753 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified1.329-4.554 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
UrineDetected and Quantified0.428-0.707 umol/mmol creatinineAdult (>18 years old)MaleBrunner Syndrome details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Yonekura T, Kamata S, Wasa M, Okada A, Yamatodani A, Watanabe T, Wada H: Simultaneous determination of plasma phenethylamine, phenylethanolamine, tyramine and octopamine by high-performance liquid chromatography using derivatization with fluorescamine. J Chromatogr. 1988 Jun 3;427(2):320-5. [PubMed:3137238 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
  2. De Angelis M, Vannini L, Di Cagno R, Cavallo N, Minervini F, Francavilla R, Ercolini D, Gobbetti M: Salivary and fecal microbiota and metabolome of celiac children under gluten-free diet. Int J Food Microbiol. 2016 Dec 19;239:125-132. doi: 10.1016/j.ijfoodmicro.2016.07.025. Epub 2016 Jul 19. [PubMed:27452636 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Ulcerative colitis
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Crohn's disease
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Brunner Syndrome
  1. Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]
Associated OMIM IDs
DrugBank IDDB08841
Phenol Explorer Compound IDNot Available
FooDB IDFDB000433
KNApSAcK IDC00001435
Chemspider ID5408
KEGG Compound IDC00483
BioCyc IDTYRAMINE
BiGG ID35110
Wikipedia LinkTyramine
METLIN ID60
PubChem Compound5610
PDB IDNot Available
ChEBI ID15760
Food Biomarker OntologyNot Available
VMH IDTYM
MarkerDB IDMDB00000142
Good Scents IDNot Available
References
Synthesis ReferenceWang, Yalou; Xie, Dongmei. Improved synthesis method of tyramine. Zhongguo Yaowu Huaxue Zazhi (1994), 4(2), 128-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tyce GM, Stockard J, Sharpless NS, Muenter MD: Excretion of amines and their metabolites by two patients in hepatic coma treated with L-dopa. Clin Pharmacol Ther. 1983 Sep;34(3):390-8. [PubMed:6883916 ]
  2. Jacob G, Costa F, Vincent S, Robertson D, Biaggioni I: Neurovascular dissociation with paradoxical forearm vasodilation during systemic tyramine administration. Circulation. 2003 May 20;107(19):2475-9. Epub 2003 Apr 21. [PubMed:12707242 ]
  3. Nakai T, Yamada R: Basic and clinical reevaluation of tyramine and histamine tests for the investigation of adrenomedullary sympathetic functions. J Clin Endocrinol Metab. 1983 Jul;57(1):19-23. [PubMed:6853676 ]
  4. Jayanthi LD, Balasubramanian N, Balasubramanian AS: Cholinesterases exhibiting aryl acylamidase activity in human amniotic fluid. Clin Chim Acta. 1992 Feb 14;205(3):157-66. [PubMed:1349516 ]
  5. Watson DG, Midgley JM, Chen RN, Huang W, Bain GM, McDonald NM, Reid JL, McGhee CN: Analysis of biogenic amines and their metabolites in biological tissues and fluids by gas chromatography-negative ion chemical ionization mass spectrometry (GC-NICIMS). J Pharm Biomed Anal. 1990;8(8-12):899-904. [PubMed:2100639 ]
  6. Chalon SA, Granier LA, Vandenhende FR, Bieck PR, Bymaster FP, Joliat MJ, Hirth C, Potter WZ: Duloxetine increases serotonin and norepinephrine availability in healthy subjects: a double-blind, controlled study. Neuropsychopharmacology. 2003 Sep;28(9):1685-93. Epub 2003 May 28. [PubMed:12784100 ]
  7. Yin SJ, Lee SC: Tyramine interference in assay of serum dopamine-beta-hydroxylase. Clin Chem. 1977 Mar;23(3):617-8. [PubMed:319927 ]
  8. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [PubMed:8255370 ]
  9. Markianos E, Backman H: Diurnal changes in dopamine-beta-hydroxylase, homovanillic acid and 3-methoxy-4-hydroxyphenylglycol in serum of man. J Neural Transm. 1976;39(1-2):79-93. [PubMed:988114 ]
  10. Causon RC, Brown MJ: Measurement of tyramine in human plasma, utilising ion-pair extraction and high-performance liquid chromatography with amperometric detection. J Chromatogr. 1984 Sep 14;310(1):11-7. [PubMed:6501508 ]
  11. Lin J, Cashman JR: Detoxication of tyramine by the flavin-containing monooxygenase: stereoselective formation of the trans oxime. Chem Res Toxicol. 1997 Aug;10(8):842-52. [PubMed:9282832 ]
  12. Wolrath H, Forsum U, Larsson PG, Boren H: Analysis of bacterial vaginosis-related amines in vaginal fluid by gas chromatography and mass spectrometry. J Clin Microbiol. 2001 Nov;39(11):4026-31. [PubMed:11682525 ]
  13. Varma DR, Chemtob S: Endothelium- and beta-2 adrenoceptor-independent relaxation of rat aorta by tyramine and certain other phenylethylamines. J Pharmacol Exp Ther. 1993 Jun;265(3):1096-104. [PubMed:8389852 ]
  14. Gabastou JM, Nugon-Baudon L, Robert Y, Manuel C, Vaissade P, Bourgeon E, Sibeud M, Szylit O, Bourlioux P: [Digestive amines of bacterial origin and behavior disorders. Apropos of a case]. Pathol Biol (Paris). 1996 Apr;44(4):275-81. [PubMed:8763591 ]
  15. Hiroi T, Imaoka S, Funae Y: Dopamine formation from tyramine by CYP2D6. Biochem Biophys Res Commun. 1998 Aug 28;249(3):838-43. [PubMed:9731223 ]
  16. Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]
  17. Antal EJ, Hendershot PE, Batts DH, Sheu WP, Hopkins NK, Donaldson KM: Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine. J Clin Pharmacol. 2001 May;41(5):552-62. [PubMed:11361052 ]
  18. Balbi T, Fusco M, Vasapollo D, Boschetto R, Cocco P, Leon A, Farruggio A: The presence of trace amines in postmortem cerebrospinal fluid in humans. J Forensic Sci. 2005 May;50(3):630-2. [PubMed:15932098 ]
  19. Marcobal A, De las Rivas B, Landete JM, Tabera L, Munoz R: Tyramine and phenylethylamine biosynthesis by food bacteria. Crit Rev Food Sci Nutr. 2012;52(5):448-67. doi: 10.1080/10408398.2010.500545. [PubMed:22369263 ]

Enzymes

Enzyme Details
1. Tyrosinase
General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
Reactions
Tyramine + Oxygen + NADH + Hydrogen Ion → Dopamine + NAD + Waterdetails
Enzyme Details
2. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Tyramine + Water + Oxygen → 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
3. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Tyramine + Water + Oxygen → 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
4. Aromatic-L-amino-acid decarboxylase
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
Reactions
L-Tyrosine → Tyramine + Carbon dioxidedetails
Enzyme Details
5. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Enzyme Details
6. Membrane primary amine oxidase
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
Tyramine + Water + Oxygen → 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
7. Retina-specific copper amine oxidase
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
Tyramine + Water + Oxygen → 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
8. Alpha-2A adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
Enzyme Details
9. Alpha-2B adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
Enzyme Details
10. Trace amine-associated receptor 1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for trace amines, including beta- phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase
Gene Name:
TAAR1
Uniprot ID:
Q96RJ0
Molecular weight:
39091.3